19 Best Sights in Madeira, Portugal

At 5,963 feet, this is one of Madeira's highest mountains. On your way here, you'll travel over a barren plain above the tree line: watch for errant sheep and goats wandering across the pavement on their way to graze on stubbly gorse and bilberry. Stop in the parking lot near the top and make the short climb to the lookout (next to a giant NATO radar), where you can scan the rocky central peaks. There are often views of the clouds below (unless you're in them), but on a clear day you can see the Curral das Freiras to the southeast. Look in the other direction and try to spot the huge Penha de Águia (Eagle Rock), a giant monolith on the north coast. The trail from the lookout that crosses the narrow ridge leads to Pico Ruivo (6,102 feet), the island's highest point, winding over the second-highest point, Pico das Torres (6,073 feet), along the way—it's one of the best hikes on the island, though it is a tough 13-km (8-mile) round-trip trek, and sections are sometimes closed by landslides. You might consider taking a guided tour from one of the many outfitters in Funchal.

The island's series of lofty peaks make for great exploring. The summit of Pico do Castelo, at 1,433 feet, has a small 16th-century fort that provided defense against the frequent attacks of French and Algerian pirates. It's a tough climb to the top, but one that's peppered with pretty flora, from cacti to berry bushes. From the summit, the views are rewarding: below you to the west is Porto Santo Beach, and to the east is the conical shape of Pico de Baixo and the Ilhéu de Cima. From here it's an easy walk to Pico do Facho (1,552 feet), the island's highest point.

Just below Pico das Flores lies Calheta Point, where the café-restaurant O Calhetas marks the western edge of the beach. There is probably no better way to enjoy the whole island than to stop for a drink or bite to eat, then walk back along the beach during the sunset as you admire the astonishing landscape.

This narrow alley of Santa Maria in Funchal's Old Town is worth walking down for the atmosphere alone: diners eat at small sidewalk cafés (though many of them are touristy), restaurant owners beckon you in for a glass of poncha, and the smell of grilled fish fills the air. But this street holds an even greater lure, as there's colorful artwork that covers almost every door. There are more than 200 paintings, depicting everything from bookshelves to musicians, created by local artists in an attempt to revitalise the area. Go early if you want to capture the paintings on camera as the street can get busy towards the afternoon.

Dating back to the 19th century, this working sugar cane factory is at its liveliest in April and May, right after the harvest that leaves a honey-like scent hanging in the air. You can take a self-guided tour to see how the local rums and liqueurs are made, then sample a few in the tasting room for a small fee.

A visit to the working sugar cane mill is a reminder that the industry once played a pivotal role in the region. The mill operates during April and May, immediately after the sugar cane harvest, but a visit any time of year will let you see the various stages of the steam-driven production. After walking around the mill, you can finish up in the Rum House to sample some of the beverages made with the crop.

Near the village of Camacha, this spring once had the purest water on the island, which is why it was used for medical treatments. The water does not spring forth with such abundance today, but is still considered sacred by locals. To reach the spring, drive west out of the village along the coastal road.

The robust yellow fortaleza dates to 1614, if not earlier, when French corsairs began to threaten Funchal's coveted deepwater harbor. Thanks to continuous use—by British troops when their nation was allied with Portugal against Napoléon, and during the visit of Portuguese King Dom Carlos in 1901—much of the military stronghold has been preserved, though it's now a bit decrepit. You can wander around the ramparts, which offer interesting views over the old town and sea below.

One of your first stops on Porto Santo should be at the Portela viewpoint, which overlooks the harbor, the town, and the long ribbon of beach. Nearby is the hilltop Capela de Nossa Senhora da Graça, one of the oldest churches on the island, dating back to 1851.

This scenic overlook at the end of a bumpy ride off the far western end of the beach offers dramatic panoramic views of the uninhabited islet of Ilhéu de Ferro rising out of the turquoise water. Look to the west and you can also see the main island of Madeira on a clear day.

Built in the 17th century as Madeira's first fortress, the St. Lawrence Palace is still used as a military headquarters. If you make an appointment in advance, you can see the grand ballroom and other state rooms filled with sumptuous works of art and antique furniture.

Abloom with flowers all year-round, Santa Catarina Park covers an area of nearly nine acres, making it one of the largest parks on the island. It offers fantastic views over Funchal and its bay up to the Ponta do Garajau. In the center of the park rests the tiny Capela de Santa Catarina (St. Catherine's Chapel), built by Madeira's discoverer João Gonçalves Zarco in 1425. Just above the park is a pink mansion called Quinta Vigia, the residence of the president of Madeira—it's closed to the public but you can visit its 18th-century chapel, lined with beautiful tiles.

About 5 km (3 miles) west of Santana is a detour where the road quickly turns into a rough mountain track. Along a trail that passes by gorse bushes, the route leads into a wonderful forest. There are picnic tables and restrooms at the thatched-roof Casa das Queimadas, which is used by forest rangers. This marks the start of a great walk to Caldeirão Verde, a three- to four-hour round-trip hike to a dramatic waterfall.

Five kilometers (3 miles) west of Santana is a detour where the road quickly turns into a rough mountain track. Along a trail that passes by gorse bushes, hydrangeas, and wildflowers, the route leads right into a wonderful forest. There are picnic tables and toilet facilities at the thatched-roof Casa das Queimadas, which is used by forest rangers. This marks the start of a great levada walk to Caldeirão Verde, a three- to four-hour round-trip hike to a dramatic waterfall.

Porto da Cruz overlooks Penha de Águia, a rocky crag whose sheer cliffs tower over the neighboring village of São Roque do Faial. You can walk the steep path to the top in two or three hours, though the climb is tough and often slippery.

With golden sand shipped in from Morocco, this calm, sheltered beach makes for enjoyable ocean swimming and strolling in the gentle surf. There isn't any shade, but you can rent beach chairs and umbrellas. Summer weekends can be extremely busy with sunbathers, who crowd onto every inch of sand. Amenities: food and drink; lifeguards; parking (fee); showers; toilets; water sports. Best for: swimming; walking.

One of the most popular beaches in Madeira, Praia de Machico has calm, warm waters that are perfect for swimming. Swaying palms and rugged hills make for a picturesque backdrop. The busy promenade extending around the beach lends itself to great people-watching. Machico provides more amenities than most Madeira beaches, with two kiddie pools, chair and umbrella rentals, and a variety of water sports. There are several snack bars and restaurants, plus an excellent ice cream kiosk on the water's edge. Amenities: food and drink; lifeguards; parking (no fee); showers; toilets; water sports. Best for: partiers; swimming; walking.

Renowned for its ceiling with intricate geometric designs of inlaid ivory, Funchal's cathedral dates from 1514 and reveals an Arabic influence throughout. Don't miss the elaborately carved and gilded choir stalls in the side entrance and in the chancel (they depict the prophets and the apostles), or the intricate tile work at the side entrance and in the belfry.